Structure of 27644-00-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 27644-00-4 |
Formula : | C20H16O |
M.W : | 272.34 |
SMILES Code : | O=C(C1=CC=CC=C1)CC2=CC=C(C3=CC=CC=C3)C=C2 |
MDL No. : | MFCD00998776 |
InChI Key : | HZXXIQLDHPWKLO-UHFFFAOYSA-N |
Pubchem ID : | 296761 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 21 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.05 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 86.56 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.85 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.81 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.78 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.48 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.39 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.46 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.93 |
Solubility | 0.00321 mg/ml ; 0.0000118 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.9 |
Solubility | 0.00342 mg/ml ; 0.0000126 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.78 |
Solubility | 0.00000448 mg/ml ; 0.0000000164 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.55 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.94 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.9% | With hydrogenchloride; In ethanol; water; for 96h;Reflux; | [00163] To a solution of 2-(biphenyl-4-yl)- l-phenylethanone (Intermediate 5) (430 mg, 1.57 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (333 mg, 1.57 mmol), and urea (217 mg, 4.71 mmol) in 20 mL of ethanol was added 0.2 mL of concentrated HCl, the mixture was stirred at reflux for 4 days. After the solvent was removed under reduced pressure, the residue was purified by column chromatography on silica gel (PE : EtOAc = 3: 1-0: 1) and thin layer chromatography (PE:EtOAc = 1 :2) to give Compound 18 (23 mg, yield 2.9%). 1H NMR (CD3OD 400 MHz TMS): delta 7.61 (d, J = 2.0 Hz, 1H), 7.49 (d, J = 7.2 Hz, 2H), 7.38-7.27 (m, 10H), 7.02 (s, 1H), 6.98 (d, J = 8.0 Hz, 2H), 5.23 (s, 1H), 4.02-3.99 (m, 2H), 1.38 (t, J = 6.8 Hz, 3H); MS (ESI): mJz 508.2 [M+l]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.7% | In tetrahydrofuran; at -78℃; for 3h;Inert atmosphere; | [00350] Step 2: Under N2, to a mixture of 2-(biphenyl-4-yl)-N-methoxy-N- methylacetamide (500 mg, 1.96 mmol) in anhydrous THF was added phenylmagnesium bromide (5 mL, 5 mmol) at -78C, and the mixture was stirred for 3 hours. When TLC indicated that the starting material was consumed, the reaction mixture was diluted with EtOAc, washed with water and brine, concentrated, and purified by column chromatography (PE : EtOAc = 20 : 1) to give Intermediate 5 (430 mg, yield 80.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With selenium; ammonium cerium (IV) nitrate; In 1,4-dioxane; at 100℃; for 12h;Sealed tube; | <strong>[27644-00-4]2-(p-phenylphenyl)acetophenone</strong> 85.2 mg (0.30 mmol), selenium powder 4.8 mg (0.06 mmol),CAN 411 mg (0.75 mmol) was sequentially added to a 25 mL pressure-resistant sealed vessel, and 3 mL of 1,4-dioxane was added. The mixture was stirred at 100 C. The reaction was followed by TLC. After 12 hours, the reaction was diluted with 10 mL of dichloromethane. The filtrate was filtered to obtain a clear solution. The organic solvent was distilled off and the residue was purified on a silica gel column using column chromatography. (eluent ratio: petroleum ether to ethyl acetate volume ratio 20:1) was separated, and the eluate was collected to evaporate the solvent to obtain 2-phenyl-9,10-phenanthrenequinone 42 mg (49% yield) as a red-brown solid. . |
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